Research on Au(I)-catalyzed ene-yne cycloisomerization for construction of quassinoid scaffold

Yuta Oki; Masahisa Nakada

doi:10.1016/j.tetlet.2018.01.069

Research on Au(I)-catalyzed ene-yne cycloisomerization for construction of quassinoid scaffold

Yuta Oki, Masahisa Nakada^*

^*Corresponding author for this work

School of Advanced Science and Engineering

Research output: Contribution to journal › Article › peer-review

4 Citations (Scopus)

Abstract

Compounds that undergo Au(I)-catalyzed cycloisomerizations affording tetracyclic products that can be converted into compounds with the skeleton of bruceantin are described. The Au(I)-catalyzed cycloisomerizations reported herein are hindered by a 1,3-diaxial interaction between the substituent and the methyl group in the transition state. The use of small substituents was found to increase the yield of the desired product, while the reaction of substrates with large substituents afford undesired constitutional isomers.

Original language	English
Pages (from-to)	926-929
Number of pages	4
Journal	Tetrahedron Letters
Volume	59
Issue number	10
DOIs	https://doi.org/10.1016/j.tetlet.2018.01.069
Publication status	Published - 2018 Mar 7

Keywords

Au(I)-catalysis
Bruceantin
Ene-yne cycloisomerization
Quassinoid
Stereoselective

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tetlet.2018.01.069

Cite this

@article{9c215981b52f4b97b6aa074624fb7889,

title = "Research on Au(I)-catalyzed ene-yne cycloisomerization for construction of quassinoid scaffold",

abstract = "Compounds that undergo Au(I)-catalyzed cycloisomerizations affording tetracyclic products that can be converted into compounds with the skeleton of bruceantin are described. The Au(I)-catalyzed cycloisomerizations reported herein are hindered by a 1,3-diaxial interaction between the substituent and the methyl group in the transition state. The use of small substituents was found to increase the yield of the desired product, while the reaction of substrates with large substituents afford undesired constitutional isomers.",

keywords = "Au(I)-catalysis, Bruceantin, Ene-yne cycloisomerization, Quassinoid, Stereoselective",

author = "Yuta Oki and Masahisa Nakada",

note = "Funding Information: We acknowledge supports of the Materials Characterization Central Laboratory, Waseda University – Japan, for characterization of new compounds. This work was financially supported in part by the Grant-in-Aid for Scientific Research on Innovative Areas 2707 Middle molecular strategy from MEXT – Japan and a Waseda University Grant for Special Research Projects. A Publisher Copyright: {\textcopyright} 2018 Elsevier Ltd",

year = "2018",

month = mar,

day = "7",

doi = "10.1016/j.tetlet.2018.01.069",

language = "English",

volume = "59",

pages = "926--929",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "10",

}

TY - JOUR

T1 - Research on Au(I)-catalyzed ene-yne cycloisomerization for construction of quassinoid scaffold

AU - Oki, Yuta

AU - Nakada, Masahisa

N1 - Funding Information: We acknowledge supports of the Materials Characterization Central Laboratory, Waseda University – Japan, for characterization of new compounds. This work was financially supported in part by the Grant-in-Aid for Scientific Research on Innovative Areas 2707 Middle molecular strategy from MEXT – Japan and a Waseda University Grant for Special Research Projects. A Publisher Copyright: © 2018 Elsevier Ltd

PY - 2018/3/7

Y1 - 2018/3/7

N2 - Compounds that undergo Au(I)-catalyzed cycloisomerizations affording tetracyclic products that can be converted into compounds with the skeleton of bruceantin are described. The Au(I)-catalyzed cycloisomerizations reported herein are hindered by a 1,3-diaxial interaction between the substituent and the methyl group in the transition state. The use of small substituents was found to increase the yield of the desired product, while the reaction of substrates with large substituents afford undesired constitutional isomers.

AB - Compounds that undergo Au(I)-catalyzed cycloisomerizations affording tetracyclic products that can be converted into compounds with the skeleton of bruceantin are described. The Au(I)-catalyzed cycloisomerizations reported herein are hindered by a 1,3-diaxial interaction between the substituent and the methyl group in the transition state. The use of small substituents was found to increase the yield of the desired product, while the reaction of substrates with large substituents afford undesired constitutional isomers.

KW - Au(I)-catalysis

KW - Bruceantin

KW - Ene-yne cycloisomerization

KW - Quassinoid

KW - Stereoselective

UR - http://www.scopus.com/inward/record.url?scp=85041539318&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85041539318&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2018.01.069

DO - 10.1016/j.tetlet.2018.01.069

M3 - Article

AN - SCOPUS:85041539318

SN - 0040-4039

VL - 59

SP - 926

EP - 929

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 10

ER -

Research on Au(I)-catalyzed ene-yne cycloisomerization for construction of quassinoid scaffold

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this